New indigoid dyestuffs



Patented Nov. 25, 1930 i UNITED STATES WILHELM BAUER, F'winsnonr'barman-mama, nn WILHELM nnnniunrnn Ann THEODOR NOCKEN, orLnvEnK snN-oN-THE-nntrnn, GERMANY, ASSIGNORS T0 GENERAL ANILINE WORKS;WA

me, OF NEW YORK, n Y.,' A CORPORATION OF DELA- NEW INDIGOID DYESTUFF SNo Drawing. Application. filed May 9, 1927, Serial no. 190,132, anq inGermany June 11, 1926.

The present invention relates'to new indigoid dyestuffs of the generalformula wherein. X stands for an alkyl residue, Y for hydrogen or anyother substituent and Z represents a halogen atom. These new dyestufismay be prepared by causing a reactive wderivative of a 2.3-naphthisatinsubstituted in the 1-position by halogen to be acted upon by a monoalkyl ether of the'1.4--dihydr0xynaphthalene or such a derivativethereof, which is not substituted in the ortho position i to thehydroxyl group.

(1) 310 parts of brominated-l-chloro-2.3- naphthisatin of the probableformula having a melting point of 313 C. and which is obtainable bytreating 1-chloro-2.3-naph- .40 thisatin in nitrobenzene solution withone molecule of bromine as described in U. S.

Patent No. 1,083,518, are converted into the (Jr-chloride by heatingwith 2&0 parts of phosphorous pentachloride in 5000 parts of chloro- 4.5benzene. The resulting product is condensed with a solution of 2001parts otd-methoxy-l naphthol chlorobenzene. The dyestufls whichpossessesflprobably the formula is filtered from the cooled reactionmixture, washed and dried. The new product is ob-, tained in the form ofa greenish blue crystalline powder, whichis sparingly soluble in organicsolvents in the cold, difficultly soluble in hot nitro-benzene, givingabluish-green color and soluble" in concentrated sulfuric acid with agreen coloration. Hydrosulfite and caustic soda lye produce areddish-brown colored vat from which textile fibres are dyed afteroxidation in very pure yellowish-green shades of excellent fastnessproperties, esper. cially of apartic ular fastness to chlorine.

ifldfhen using instead 1 of .brominated-lchloro-2.3-naphthisatin, the.brominated 1- broino- .3-naphthisatin or the nitro product, whichis-easily obtainable by nitration of bromo-l-chloroQBFnaphthi atin ingconcentrated sulfuric acid (small yellow needles melting above 280. C.)still yellower green shades result.- Instead of{lvlllQlJhQXY-l-HELPhthol other analogous ethers canbe employed.

By theapplication of 1-,cl1olor-2.3-naphthisatin a somewhat bluer greenis obtained. We claim 1. As newproducts indigoid diyestufis of thegeneral formula:

where Y stands for hydrogen or any other EN 0-FF lCE= a g ISOsubstituent, which dyestuffs are generally dark bluish-green crystallinepowders soluble with difficulty in cold concentrated sulfuric acid witha green coloration, dyeing the textile fibre from a reddish-brownhydrosulfite vat fast green shades, and which may be obtained bycondensing the l-methoxy-l-naphthol with a reactive Jr-derivative of anl-chloro-Q.3-naphthisatin.

2-. As a new product an indigoid dyestuff of the general formula whereinX stands for an alkyl residue, Y for hydrogen or any other substituentand Z represents a halogen atom, which dyestuffs are generally darkbluish-green crystalline powders soluble with difliculty in coldconcentrated sulfuric acid with a green coloration, dyeing the textilefibre from a reddish-brown hydrosulfite vat fast green shades.

4. As new products, the compounds of the general formula:

wherein X stands for an alkyl residue, Y for hydrogen or any othersubstituent and Z represents a halogen atom, which dyestuffs aregenerally dark bluislrgreen crystalline powders soluble with difficultyin cold concentrated sulfuric acid with a green coloration,

dyeing the textile fibre from a reddish-brown hydrosulfite vat fastgreen shades.

In testimony whereof, we afiiX our signatures.

WILHELM BAUER. WILHELM NEELMEIER. THEODOR NOCKEN.

